How does KAYAK find such low prices on flights from Hawaii to Chicago?

KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.

How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?

KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.

What is the Hacker Fare option on flights from Hawaii to Chicago?

Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.

What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?

Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

$113 CHEAP FLIGHTS from Hawaii to Chicago

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Cheap Flights from Hawaii to Chicago

Discover the best prices for you by selecting your travel dates on KAYAK.

Round-trip

One-way

Last minute

Direct

Recent round-trip flight deals from Hawaii to Chicago

Thu, Oct 22 - Mon, Oct 26

12:35 pm - 5:40 amLIH Lihue-ORD Chicago O'Hare Intl

12h 05m1 stop Seattle/Tacoma Intl

6:00 am - 2:45 pmORD Chicago O'Hare Intl-LIH Lihue

13h 45m1 stop Seattle/Tacoma Intl

$388Alaska Airlines

Thu, Oct 22 - Mon, Oct 26

12:35 pm - 5:40 amLIH Lihue-ORD Chicago O'Hare Intl

12h 05m1 stop Seattle/Tacoma Intl

7:49 pm - 11:27 amORD Chicago O'Hare Intl-LIH Lihue

20h 38m1 stop San Diego

$388Multiple Airlines

Thu, Oct 22 - Mon, Oct 26

12:35 pm - 5:40 amLIH Lihue-ORD Chicago O'Hare Intl

12h 05m1 stop Seattle/Tacoma Intl

7:49 pm - 3:39 pmORD Chicago O'Hare Intl-LIH Lihue

24h 50m2 stops San Diego Kahului

$393Multiple Airlines

Thu, Oct 1 - Mon, Oct 5

1:25 pm - 5:00 amLIH Lihue-ORD Chicago O'Hare Intl

10h 35m1 stop Los Angeles

5:59 am - 2:51 pmORD Chicago O'Hare Intl-LIH Lihue

13h 52m1 stop Phoenix Sky Harbor Intl

$406American Airlines

Fri, Oct 2 - Tue, Oct 13

9:54 pm - 1:29 pmLIH Lihue-ORD Chicago O'Hare Intl

10h 35m1 stop Seattle/Tacoma Intl

8:29 am - 7:19 pmORD Chicago O'Hare Intl-LIH Lihue

15h 50m2 stops Detroit Metropolitan Wayne County Seattle/Tacoma Intl

$440Delta

Tue, Oct 27 - Tue, Nov 17

9:06 pm - 4:53 pmKOA Kona Intl-ORD Chicago O'Hare Intl

14h 47m1 stop Seattle/Tacoma Intl

7:35 am - 3:00 pmORD Chicago O'Hare Intl-KOA Kona Intl

11h 25m1 stop Salt Lake City

$470Delta

Wed, Nov 11 - Mon, Nov 16

11:40 am - 5:55 amKOA Kona Intl-MDW Chicago Midway

14h 15m2 stops Honolulu Oakland

5:20 am - 2:15 pmMDW Chicago Midway-KOA Kona Intl

12h 55m2 stops Phoenix Sky Harbor Intl Kahului

$470Southwest

Wed, Nov 11 - Mon, Nov 16

11:34 am - 1:17 pmKOA Kona Intl-ORD Chicago O'Hare Intl

21h 43m1 stop San Diego

2:15 pm - 3:52 pmORD Chicago O'Hare Intl-KOA Kona Intl

29h 37m1 stop San Diego

$470Alaska Airlines

Tue, Oct 27 - Tue, Nov 3

1:10 pm - 5:55 amHNL Honolulu-MDW Chicago Midway

11h 45m1 stop Oakland

10:00 am - 9:20 pmMDW Chicago Midway-HNL Honolulu

15h 20m2 stops Las Vegas Harry Reid Intl San Diego

$476Southwest

Tue, Oct 27 - Tue, Nov 3

6:01 pm - 7:00 amHNL Honolulu-ORD Chicago O'Hare Intl

7h 59mnonstop

10:00 am - 3:18 pmORD Chicago O'Hare Intl-HNL Honolulu

9h 18mnonstop

$565American Airlines

Recent last minute flight deals from Hawaii to Chicago

Wed, Sep 23 - Wed, Sep 30

1:25 pm - 5:59 amLIH Lihue-ORD Chicago O'Hare Intl

11h 34m1 stop Los Angeles

6:59 am - 3:02 pmORD Chicago O'Hare Intl-LIH Lihue

13h 03m1 stop Phoenix Sky Harbor Intl

$454American Airlines

Wed, Sep 23 - Thu, Oct 1

1:25 pm - 5:59 amLIH Lihue-ORD Chicago O'Hare Intl

11h 34m1 stop Los Angeles

6:59 am - 3:02 pmORD Chicago O'Hare Intl-LIH Lihue

13h 03m1 stop Phoenix Sky Harbor Intl

$454American Airlines

Wed, Sep 23 - Wed, Sep 30

9:54 pm - 6:04 pmLIH Lihue-ORD Chicago O'Hare Intl

15h 10m2 stops Seattle/Tacoma Intl Salt Lake City

12:50 pm - 7:10 pmORD Chicago O'Hare Intl-LIH Lihue

11h 20m1 stop Seattle/Tacoma Intl

$460Delta

Wed, Sep 23 - Wed, Sep 30

9:54 pm - 6:01 pmLIH Lihue-ORD Chicago O'Hare Intl

15h 07m1 stop Seattle/Tacoma Intl

7:45 am - 7:10 pmORD Chicago O'Hare Intl-LIH Lihue

16h 25m2 stops Salt Lake City Seattle/Tacoma Intl

$460Delta

Tue, Sep 22 - Tue, Sep 29

8:25 pm - 1:30 pmLIH Lihue-MDW Chicago Midway

12h 05m1 stop Las Vegas Harry Reid Intl

10:15 am - 4:10 pmMDW Chicago Midway-LIH Lihue

10h 55m1 stop Oakland

$524Southwest

Tue, Sep 22 - Tue, Sep 29

8:25 pm - 1:30 pmLIH Lihue-MDW Chicago Midway

12h 05m1 stop Las Vegas Harry Reid Intl

6:40 am - 4:10 pmMDW Chicago Midway-LIH Lihue

14h 30m2 stops Denver Intl Oakland

$530Southwest

Sat, Sep 19 - Wed, Sep 23

2:56 pm - 12:07 pmHNL Honolulu-ORD Chicago O'Hare Intl

16h 11m1 stop Seattle/Tacoma Intl

1:03 pm - 9:24 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 21m1 stop Seattle/Tacoma Intl

$630Alaska Airlines

Fri, Sep 18 - Thu, Sep 24

12:30 pm - 1:22 pmHNL Honolulu-ORD Chicago O'Hare Intl

19h 52m1 stop San Diego

7:20 am - 3:55 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 35m1 stop San Diego

$630Multiple Airlines

Sat, Sep 19 - Wed, Sep 23

10:43 am - 6:20 amHNL Honolulu-ORD Chicago O'Hare Intl

14h 37m2 stops Lihue Seattle/Tacoma Intl

1:03 pm - 9:24 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 21m1 stop Seattle/Tacoma Intl

$667Multiple Airlines

Sat, Sep 19 - Mon, Sep 21

2:56 pm - 12:07 pmHNL Honolulu-ORD Chicago O'Hare Intl

16h 11m1 stop Seattle/Tacoma Intl

7:20 am - 3:55 pmORD Chicago O'Hare Intl-HNL Honolulu

13h 35m1 stop San Diego

$680Alaska Airlines

Useful Info

Low season	January
High season	December
Cheapest flight	$113

Best time to beat the crowds with an average 30% drop in price.

Most popular time to fly and prices are also 2% lower on average.

Flight from Honolulu to Chicago Midway Airport

How does KAYAK find such low prices on flights from Hawaii to Chicago?
KAYAK is a travel search engine. That means we look across the web to find the best prices we can find for our users. With over 2 billion flight queries processed yearly, we are able to display a variety of prices and options on flights from Hawaii to Chicago.
How does KAYAK's flight Price Forecast tool help me choose the right time to buy my flight ticket from Hawaii to Chicago?
KAYAK’s flight Price Forecast tool uses historical data to determine whether the price for a flight to Chicago from Hawaii is likely to change within 7 days, so travelers know whether to wait or book now.
What is the Hacker Fare option on flights from Hawaii to Chicago?
Hacker Fares allow you to combine one-way tickets in order to save you money over a traditional round-trip ticket. You could then fly to Chicago with an airline and back to Hawaii with another airline.
What is KAYAK's "flexible dates" feature and why should I care when looking for a flight from Hawaii to Chicago?
Sometimes travel dates aren't set in stone. If your preferred travel dates have some wiggle room, flexible dates will show you all the options when flying to Chicago from Hawaii up to 3 days before/after your preferred dates. You can then pick the flights that suit you best.

Merrillville

Hammond

Saint Joseph

Portage

Lansing

Valparaiso

Schererville

Chesterton

Munster

Porter

Monticello

Saint John

Griffith

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$113 Find Cheap Flights from Hawaii to Chicago - Compare and Save

Cheap Flights from Hawaii to Chicago

Recent round-trip flight deals from Hawaii to Chicago

Recent one-way flight deals from Hawaii to Chicago

Recent last minute flight deals from Hawaii to Chicago

Recent direct flight deals from Hawaii to Chicago

Good to know

Low season

High season

Cheapest flight

FAQs for booking flights from Hawaii to Chicago

Traveling to a place near Chicago?

More options for your flight to Chicago

Complete your trip to Chicago with a hotel stay or car rental

Cabin class types available on flights to Hawaii

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